JP2011144274A - Liquid crystal composition and liquid crystal display element - Google Patents

Liquid crystal composition and liquid crystal display element Download PDF

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JP2011144274A
JP2011144274A JP2010006537A JP2010006537A JP2011144274A JP 2011144274 A JP2011144274 A JP 2011144274A JP 2010006537 A JP2010006537 A JP 2010006537A JP 2010006537 A JP2010006537 A JP 2010006537A JP 2011144274 A JP2011144274 A JP 2011144274A
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liquid crystal
component
crystal composition
carbons
composition according
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JP5531632B2 (en
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Norikazu Hattori
Eriko Kurihara
憲和 服部
衣理子 栗原
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Chisso Petrochemical Corp
Jnc Corp
Jnc株式会社
チッソ石油化学株式会社
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    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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    • C09K19/3001Cyclohexane rings
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    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001Cyclohexane rings
    • C09K19/3066Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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    • C09K19/3001Cyclohexane rings
    • C09K19/3066Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3425Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/10Liquid crystal optical display having layer of specified composition
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/10Liquid crystal optical display having layer of specified composition
    • Y10T428/1036Liquid crystal optical display having layer of specified composition with viewing layer of specified composition

Abstract

<P>PROBLEM TO BE SOLVED: To provide a liquid crystal composition satisfying at least one characteristic or having suitable balance of at least two characteristics of characteristics such as a high upper limit temperature of a nematic phase, a low lower limit temperature of the nematic phase, low viscosity, suitable optical anisotropy, negatively large dielectric anisotropy, high specific resistance, high stability to UV, high stability to heat, and to provide an active matrix (AM) element having a short response time, a high voltage holding ratio, a high contrast ratio, a long life and the like. <P>SOLUTION: The liquid crystal composition includes a specified tetra-cyclic compound having a high upper limit temperature and negatively large dielectric anisotropy as a first component and a bi-cyclic compound having low viscosity as a second component, and may respectively contain a specified compound having negatively large dielectric anisotropy as a third component, a specified compound having low viscosity as a fourth component and a specified compound having negatively large dielectric anisotropy as a fifth component to make the liquid crystal composition having the negative dielectric anisotropy and the liquid crystal element contains the composition. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a liquid crystal composition suitable mainly for an AM (active matrix) device and the like, and an AM device containing the composition. In particular, the present invention relates to a liquid crystal composition having a negative dielectric anisotropy, and relates to an IPS (in-plane switching) mode, VA (vertical alignment) mode, or PSA (polymer sustained alignment) mode element containing the composition.

  In the liquid crystal display element, the classification based on the operation mode of the liquid crystal includes PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS ( in-plane switching), VA (vertical alignment), PSA (Polymer sustained alignment) mode, and the like. The classification based on the element driving method is PM (passive matrix) and AM (active matrix). PM is classified into static and multiplex, and AM is classified into thin film transistor (TFT), metal insulator metal (MIM), and the like. TFTs are classified into amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to the manufacturing process. The classification based on the light source includes a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both natural light and backlight.

  These devices contain a liquid crystal composition having appropriate characteristics. This liquid crystal composition has a nematic phase. In order to obtain an AM device having good general characteristics, the general characteristics of the composition are improved. The relationships in the two general characteristics are summarized in Table 1 below. The general characteristics of the composition will be further described based on a commercially available AM device. The temperature range of the nematic phase is related to the temperature range in which the device can be used. A preferred maximum temperature of the nematic phase is about 70 ° C. or more, and a preferred minimum temperature of the nematic phase is about −10 ° C. or less. The viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. Therefore, a small viscosity in the composition is preferred. Small viscosities at low temperatures are more preferred.

  The optical anisotropy of the composition is related to the contrast ratio of the device. The product (Δn × d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the device is designed to maximize the contrast ratio. The appropriate product value depends on the type of operation mode. The range is about 0.30 μm to about 0.40 μm for the VA mode device, and the range is about 0.20 μm to about 0.30 μm for the IPS mode device. In this case, a composition having a large optical anisotropy is preferable for a device having a small cell gap. The dielectric anisotropy having a large absolute value in the composition contributes to a low threshold voltage, a small power consumption and a large contrast ratio in the device. Therefore, a dielectric anisotropy having a large absolute value is preferable. A large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a high temperature in the initial stage is preferable. A composition having a large specific resistance not only at room temperature but also at a high temperature after being used for a long time is preferable. The stability of the composition against ultraviolet rays and heat is related to the lifetime of the liquid crystal display device. When their stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM device used in a liquid crystal projector, a liquid crystal television, and the like.

  In an AM device having a TN mode, a composition having a positive dielectric anisotropy is used. On the other hand, a composition having negative dielectric anisotropy is used for an AM device having a VA mode. In an AM device having an IPS mode, a composition having a positive or negative dielectric anisotropy is used. In an AM device having a PSA mode, a composition having a positive or negative dielectric anisotropy is used. An example of a liquid crystal composition having a negative dielectric anisotropy is disclosed in Patent Document 1 described below.

International Publication 2009/034867 Pamphlet

  Desirable AM elements have characteristics such as a wide usable temperature range, a short response time, a large contrast ratio, a low threshold voltage, a large voltage holding ratio, and a long lifetime. A shorter response time is desirable even at 1 millisecond. Therefore, desirable properties of the composition include a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, a large positive or negative dielectric anisotropy, a large specific resistance, and a high resistance to ultraviolet light. High stability, high heat stability, etc.

  One object of the present invention is to provide a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, and a high stability to ultraviolet light. The liquid crystal composition satisfies at least one characteristic in characteristics such as high stability to heat. Another object is a liquid crystal composition having an appropriate balance with respect to at least two properties, particularly a liquid crystal composition satisfying a high maximum temperature and a small viscosity. Another object is a liquid crystal display device containing such a composition. Another object is a composition having a small optical anisotropy, or a suitable optical anisotropy that is a large optical anisotropy, a negative large dielectric anisotropy, a high stability to ultraviolet rays, etc., and a short The AM device has a response time, a large voltage holding ratio, a large contrast ratio, a long lifetime, and the like.

Contains at least one compound selected from the group of compounds represented by formula (1) as the first component and at least one compound selected from the group of compounds represented by formula (2) as the second component And a liquid crystal composition having negative dielectric anisotropy, and a liquid crystal display device containing the composition.

Here, R 1 , R 2 , R 3 , and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or any hydrogen is fluorine. 2 to 12 carbons alkenyl substituted with; ring A and ring B are independently 1,4-cyclohexylene or 1,4-phenylene; either ring C or ring D is 2,3-difluoro-1,4-phenylene, the other is 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 3 are independently a single bond, ethylene, or difluoromethyleneoxy Z 2 is methyleneoxy, difluoromethyleneoxy, or carbonyloxy.

  The advantages of the present invention are that the upper limit temperature of the nematic phase, the lower limit temperature of the nematic phase, the small viscosity, the appropriate optical anisotropy, the negative dielectric constant anisotropy, the large specific resistance, the high stability to ultraviolet rays, the heat It is a liquid crystal composition satisfying at least one of the properties such as high stability against the liquid crystal. One aspect of the present invention is a liquid crystal composition having an appropriate balance regarding at least two properties. Another aspect is a liquid crystal display device containing such a composition. Other aspects are compositions with suitable optical anisotropy, negatively large dielectric anisotropy, high stability to ultraviolet light, etc., and short response time, large voltage holding ratio, large contrast ratio, long lifetime An AM device having the above.

  Terms used in this specification are as follows. The liquid crystal composition of the present invention or the liquid crystal display device of the present invention may be abbreviated as “composition” or “device”, respectively. A liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module. “Liquid crystal compound” means a compound having a liquid crystal phase such as a nematic phase or a smectic phase, or a compound having no liquid crystal phase but useful as a component of a composition. This useful compound has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like. Optically active compounds and polymerizable compounds may be added to the composition. Even if these compounds are liquid crystal compounds, they are classified as additives here. At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as “compound (1)”. “Compound (1)” means one compound or two or more compounds represented by formula (1). The same applies to compounds represented by other formulas. “Arbitrary” indicates that not only the position but also the number is arbitrary, but the case where the number is 0 is not included.

  The upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”. The lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”. "High specific resistance" means that the composition has a large specific resistance not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase. It means having a large specific resistance even at a close temperature. "High voltage holding ratio" means that the device has a large voltage holding ratio not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase. It means having a large voltage holding ratio even at a temperature close to. When describing characteristics such as optical anisotropy, values measured by the methods described in the examples are used. The first component is one compound or two or more compounds. The “ratio of the first component” means the percentage by weight (% by weight) of the first component based on the total weight of the liquid crystal composition. The same applies to the ratio of the second component. The ratio of the additive mixed with the composition means a percentage by weight (% by weight) or a percentage by weight (ppm) based on the total weight of the liquid crystal composition.

In the chemical formulas of the component compounds, the symbol R 1 is used for a plurality of compounds. In any two of these compounds, the meaning of R 1 may be the same or different. For example, there is a case where R 1 of the compound (1) is ethyl and R 1 of the compound (1-1) is ethyl. In some cases, R 1 of compound (1) is ethyl and R 1 of compound (1-1) is propyl. This rule also applies to R 2 , Z 1 and the like.

  The present invention includes the following items.

1. Contains at least one compound selected from the group of compounds represented by formula (1) as the first component and at least one compound selected from the group of compounds represented by formula (2) as the second component And a liquid crystal composition having negative dielectric anisotropy.

Here, R 1 , R 2 , R 3 , and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or any hydrogen is fluorine. 2 to 12 carbons alkenyl substituted with; ring A and ring B are independently 1,4-cyclohexylene or 1,4-phenylene; either ring C or ring D is 2 , 3-difluoro-1,4-phenylene, the other is 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 3 are independently a single bond, ethylene, or difluoromethyleneoxy. Yes; Z 2 is methyleneoxy, difluoromethyleneoxy, or carbonyloxy.

2. Item 2. The liquid crystal composition according to item 1, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-1) to formula (1-6).

Here, R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon in which any hydrogen is replaced with fluorine. 2 to 12 alkenyl.

3. Item 3. The liquid crystal composition according to item 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-1).

4). Item 3. The liquid crystal composition according to item 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-2).

5. Items 1 to 4 wherein the proportion of the first component is in the range of 5 to 40% by weight and the proportion of the second component is in the range of 10 to 95% by weight based on the total weight of the liquid crystal composition The liquid crystal composition according to any one of the above.

6). Item 6. The liquid crystal composition according to any one of items 1 to 5, further containing at least one compound selected from the group of compounds represented by formula (3) as a third component.

Here, R 5 and R 6 are each independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine. Ring E is independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 2-fluoro-1,4-phenylene, or 2, 3-difluoro-1,4-phenylene; Z 4 is independently a single bond, ethylene, methyleneoxy, or carbonyloxy; X 1 and X 2 are independently fluorine or chlorine; Y 1 is hydrogen or methyl; p is 1 or 2, q is 0 or 1, and the sum of p and q is 2 or less.

7). Item 7. The liquid crystal composition according to item 6, wherein the third component is at least one compound selected from the group of compounds represented by formulas (3-1) to (3-20).


Here, R 5 and R 6 are each independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine. To 12 alkenyl.

8). Item 8. The liquid crystal composition according to item 7, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-1).

9. The third component is at least one compound selected from the group of compounds represented by formula (3-2) and at least one compound selected from the group of compounds represented by formula (3-5) Item 8. A liquid crystal composition according to item 7.

10. Item 8. The liquid crystal composition according to item 7, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-14).

11. Item 8. The liquid crystal composition according to item 7, wherein the third component is at least one compound selected from the group of compounds represented by formulas (3-16) to (3-19).

12 Item 12. The liquid crystal composition according to any one of items 6 to 11, wherein the ratio of the third component is in the range of 10% by weight to 70% by weight based on the total weight of the liquid crystal composition.

13. Item 13. The liquid crystal composition according to any one of items 1 to 12, further containing at least one compound selected from the group of compounds represented by formula (4) as a fourth component.

Here, R 7 and R 8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number 2 in which any hydrogen is replaced with fluorine. Ring F, ring G, and ring I are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3-fluoro-. 1,4-phenylene; Z 5 and Z 6 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy; r is 0, 1, or 2, where r is 0 , At least one of ring G and ring I is 1,4-phenylene.

14 Item 14. The liquid crystal composition according to item 13, wherein the fourth component is at least one compound selected from the group of compounds represented by formulas (4-1) to (4-12).

Here, R 7 and R 8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number 2 in which any hydrogen is replaced with fluorine. To 12 alkenyl.

15. Item 15. The liquid crystal composition according to item 14, wherein the fourth component is at least one compound selected from the group of compounds represented by formula (4-4).

16. Item 15. The liquid crystal composition according to item 14, wherein the fourth component is at least one compound selected from the group of compounds represented by formula (4-7).

17. Item 17. The liquid crystal composition according to any one of items 13 to 16, wherein the ratio of the fourth component is in the range of 5% by weight to 40% by weight based on the total weight of the liquid crystal composition.

18. Item 18. The liquid crystal composition according to any one of items 1 to 17, further containing at least one compound selected from the group of compounds represented by formula (5) as a fifth component.

Here, R 9 and R 10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having an arbitrary hydrogen substituted with fluorine. Ring J and ring K are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or 2,3-difluoro-1,4. -Phenylene; Z 7 and Z 8 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy; s and t are independently 0, 1, 2, or 3, and s And the sum of t is 3 or less.

19. Item 19. The liquid crystal composition according to item 18, wherein the fifth component is at least one compound selected from the group of compounds represented by formulas (5-1) to (5-5).

Here, R 9 and R 10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having an arbitrary hydrogen substituted with fluorine. To 12 alkenyl.

20. Item 20. The liquid crystal composition according to item 19, wherein the fifth component is at least one compound selected from the group of compounds represented by formula (5-4).

21. Item 21. The liquid crystal composition according to any one of items 18 to 20, wherein the ratio of the fifth component is in the range of 5% by weight to 30% by weight based on the total weight of the liquid crystal composition.

22. The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy (25 ° C.) at a wavelength of 589 nm is 0.08 or higher, and the dielectric anisotropy (25 ° C.) at a frequency of 1 kHz is −2 or lower. Item 22. The liquid crystal composition according to any one of items 1 to 21.

23. Item 23. A liquid crystal display device comprising the liquid crystal composition according to any one of items 1 to 22.

24. Item 24. The liquid crystal display element according to item 23, wherein the operation mode of the liquid crystal display element is a VA mode, an IPS mode, or a PSA mode, and the driving method of the liquid crystal display element is an active matrix method.

  The present invention also includes the following items. 1) The above composition further containing an optically active compound, 2) the above composition further containing an additive such as an antioxidant, an ultraviolet absorber, and an antifoaming agent, and 3) the above composition. AM device, 4) a device containing the above composition and having a mode of TN, ECB, OCB, IPS, VA, or PSA, 5) a transmissive device containing the above composition, 6) the above Use of the composition as a composition having a nematic phase, 7) Use as an optically active composition by adding an optically active compound to the above composition.

  The composition of the present invention will be described in the following order. First, the constitution of component compounds in the composition will be described. Second, the main characteristics of the component compounds and the main effects of the compounds on the composition will be explained. Third, the combination of components in the composition, the preferred ratio of the component compounds, and the basis thereof will be described. Fourth, a preferred form of the component compound will be described. Fifth, specific examples of component compounds are shown. Sixth, additives that may be mixed into the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Finally, the use of the composition will be described.

  First, the constitution of component compounds in the composition will be described. The composition of the present invention is classified into Composition A and Composition B. The composition A may further contain other liquid crystal compounds, additives, impurities and the like. The “other liquid crystal compound” is a liquid crystal compound different from the compound (1), the compound (2), the compound (3), the compound (4), and the compound (5). Such compounds are mixed into the composition for the purpose of further adjusting the properties. Among the other liquid crystal compounds, a smaller amount of cyano compound is preferable from the viewpoint of stability to heat or ultraviolet light. A more desirable ratio of the cyano compound is 0% by weight. Additives include optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, and the like. Impurities are compounds mixed in a process such as synthesis of component compounds. Even if this compound is a liquid crystal compound, it is classified as an impurity here.

  Composition B consists essentially of a compound selected from compound (1), compound (2), compound (3), compound (4), and compound (5). “Substantially” means that the composition does not contain a liquid crystal compound different from these compounds, except for additives and impurities. Composition B has fewer components than composition A. From the viewpoint of reducing the cost, the composition B is preferable to the composition A. The composition A is preferable to the composition B from the viewpoint that the physical properties can be further adjusted by mixing other liquid crystal compounds.

  Second, the main characteristics of the component compounds and the main effects of the compounds on the characteristics of the composition will be explained. The main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention. In the symbols in Table 2, L means large or high, M means moderate, and S means small or low. The symbols L, M, and S are classifications based on a qualitative comparison among the component compounds, and 0 (zero) means that the value is almost zero.

  When component compounds are mixed into the composition, the main effects of the component compounds on the properties of the composition are as follows. Compound (1) increases the maximum temperature and increases the absolute value of dielectric anisotropy. Compound (2) decreases the viscosity. Compound (3) increases the absolute value of dielectric anisotropy and decreases the minimum temperature. Compound (4) decreases the viscosity, adjusts the appropriate optical anisotropy, and decreases the minimum temperature. Compound (5) increases the absolute value of dielectric anisotropy.

  Third, the combination of components in the composition, the preferred ratio of the component compounds, and the basis thereof will be described. The combination of the components in the composition is as follows: first component + second component, first component + second component + third component, first component + second component + fourth component, first component + second component + fifth Component, first component + second component + third component + fourth component, first component + second component + third component + fifth component, first component + second component + fourth component + fifth component, And first component + second component + third component + fourth component + fifth component.

  A preferred combination of components in the composition is the first component + second component for increasing the maximum temperature, and the first component for increasing the absolute value of the dielectric anisotropy, decreasing the viscosity, or decreasing the minimum temperature. 1 component + 2nd component + 3rd component, 1st component + 2nd component + in order to increase the absolute value of dielectric anisotropy, to lower viscosity, or to adjust appropriate optical anisotropy The third component + the fourth component, and the first component + the second component + the third component + the fourth component + the fifth component in order to increase the absolute value of the dielectric anisotropy. A particularly preferred combination is first component + second component + third component + fourth component in order to lower the viscosity.

  A desirable ratio of the first component is approximately 5% by weight or more for increasing the absolute value of the dielectric anisotropy, and approximately 40% by weight or less for decreasing the minimum temperature. A more desirable ratio is in the range of approximately 10% by weight to approximately 35% by weight. A particularly preferred ratio is in the range of approximately 15% by weight to approximately 30% by weight.

  A desirable ratio of the second component is approximately 10% by weight or more for decreasing the viscosity, and approximately 95% by weight or less for decreasing the minimum temperature. A more desirable ratio is in the range of approximately 20% by weight to approximately 70% by weight for decreasing the viscosity. A particularly desirable ratio is in the range of approximately 30% by weight to approximately 60% by weight.

  A desirable ratio of the third component is approximately 10% by weight or more for increasing the absolute value of the dielectric anisotropy, and approximately 70% by weight or less for decreasing the minimum temperature. A more desirable ratio is in the range of approximately 20% by weight to approximately 60% by weight. A particularly preferred ratio is in the range of approximately 30% by weight to approximately 50% by weight.

  A desirable ratio of the fourth component is 5% by weight or more for decreasing the viscosity, and is 40% by weight or less for decreasing the minimum temperature. A more desirable ratio is from 10% by weight to 35% by weight. A particularly preferred ratio is in the range of approximately 15% by weight to approximately 30% by weight.

  A desirable ratio of the fifth component is approximately 5% by weight or more for increasing the absolute value of the dielectric anisotropy, and approximately 30% by weight or less for decreasing the minimum temperature. A more desirable ratio is in the range of approximately 10% by weight to approximately 25% by weight. A particularly preferred ratio is in the range of approximately 15% by weight to approximately 20% by weight.

Fourth, a preferred form of the component compound will be described.
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently alkyl having 1 to 12 carbons and alkoxy having 1 to 12 carbons , Alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which arbitrary hydrogen is replaced by fluorine.

Preferred R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , or R 10 are alkyl having 1 to 12 carbons for decreasing the minimum temperature or decreasing the viscosity, or Alkenyl having 2 to 12 carbons. Desirable R 5 or R 6 is alkyl having 1 to 12 carbons for decreasing the minimum temperature or decreasing the viscosity, and 1 to 12 carbons for increasing the absolute value of the dielectric anisotropy. Of alkoxy. More desirable R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , or R 10 is an alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat. It is.

  Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl. More desirable alkyl is ethyl, propyl, butyl, pentyl, or heptyl for decreasing the viscosity.

  Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.

  Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl or 3-pentenyl for decreasing the viscosity. The preferred configuration of —CH═CH— in these alkenyls depends on the position of the double bond. Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity. Cis is preferable in alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl. In these alkenyl, linear alkenyl is preferable to branching.

  Preferred examples of alkenyl in which any hydrogen is replaced by fluorine include 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4- Pentenyl, and 6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinyl and 4,4-difluoro-3-butenyl for decreasing the viscosity.

  p is 1 or 2, q is 0 or 1, and the sum of p and q is 2 or less. Preferred p is 2 for increasing the maximum temperature, and 1 for decreasing the viscosity. Preferred q is 1 for increasing the maximum temperature, and 0 for decreasing the minimum temperature. r is 0, 1, or 2. Desirable r is 1 or 2 for increasing the maximum temperature, and 0 for decreasing the viscosity. s and t are independently 0, 1, 2, or 3, and the sum of s and t is 3 or less. Preferred s or t is 2 or 3 for increasing the maximum temperature, and 1 for decreasing the viscosity.

  Ring A and ring B are independently 1,4-cyclohexylene and 1,4-phenylene. Desirable ring A or ring B is 1,4-cyclohexylene for increasing the maximum temperature, and 1,4-phenylene for increasing the optical anisotropy. One of ring C and ring D is 2,3-difluoro-1,4-phenylene, and the other is 1,4-cyclohexylene or 1,4-phenylene. Desirable ring C or ring D is 1,4-cyclohexylene for increasing the maximum temperature, and 1,4-phenylene for increasing the optical anisotropy. Particularly preferred ring C is 2,3-difluoro-1,4-phenylene for increasing the dielectric anisotropy, and particularly preferable ring D is 1,4-cyclohexylene for increasing the maximum temperature. . Ring E is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 2-fluoro-1,4-phenylene, or 2,3-difluoro-1,4-phenylene. And any two rings E when p is 2 may be the same or different. Preferred ring E is 1,4-cyclohexylene for increasing the maximum temperature, and tetrahydropyran-2,5-diyl or 2,3-difluoro-1,4-phenylene for increasing the dielectric anisotropy. It is. Ring F, Ring G, and Ring I are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3-fluoro-1,4-phenylene. Any two rings F when r is 2, may be the same or different; when r is 0, at least one of ring G and ring I is 1,4-phenylene; is there. Preferred ring F, ring G or ring I is 1,4-cyclohexylene for increasing the maximum temperature or decreasing the viscosity, and 1,4-phenylene for increasing the optical anisotropy. . Ring J and Ring K are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or 2,3-difluoro-1,4-phenylene, and s is Any two rings J when 2 or 3 may be the same or different, and any two rings J when t is 2 or 3 may be the same or different Good. Desirable ring J or ring K is 1,4-cyclohexylene for increasing the maximum temperature or decreasing the viscosity, and 1,4-phenylene for increasing the optical anisotropy.

X 1 and X 2 are independently fluorine or chlorine. Desirable X 1 or X 2 is fluorine for decreasing the viscosity.

Y 1 is hydrogen or methyl. Preferred Y 1 is hydrogen for decreasing the viscosity, and methyl for increasing the stability to ultraviolet light, heat and the like.

Z 1 and Z 3 are independently a single bond, ethylene, or difluoromethyleneoxy. Desirable Z 1 or Z 3 is a single bond for decreasing the viscosity. Z 2 is methyleneoxy, difluoromethyleneoxy, or carbonyloxy. Desirable Z 2 is carbonyloxy for increasing the maximum temperature, and methyleneoxy for decreasing the minimum temperature. Z 4 is a single bond, ethylene, methyleneoxy, or carbonyloxy, and any two Z 4 when p is 2 may be the same or different. Desirable Z 4 is a single bond for decreasing the viscosity, and methyleneoxy for increasing the dielectric anisotropy. Z 5 and Z 6 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy, and any two Z 5 when r is 2 may be the same or different. Desirable Z 5 or Z 6 is a single bond for decreasing the viscosity, and carbonyloxy for increasing the maximum temperature. Z 7 and Z 8 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy, and any two Z 7 or Z 8 when s or t is 2 or 3 may be the same May be different. Desirable Z 7 is a single bond for decreasing the viscosity, and methyleneoxy for increasing the dielectric anisotropy. Desirable Z 8 is a single bond for decreasing the viscosity, and ethylene for decreasing the minimum temperature.

Fifth, specific examples of component compounds are shown.
In the following preferable compounds, R 11 , R 12 , R 16 and R 17 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, and alkenyl having 2 to 12 carbons. R 13 and R 14 are independently straight-chain alkyl having 1 to 12 carbons and alkoxy having 1 to 12 carbons. R 15 is straight-chain alkenyl having 2 to 12 carbons. In these compounds, the configuration of 1,4-cyclohexylene is preferably trans rather than cis for increasing the maximum temperature.

  Desirable compounds (1) are from the compound (1-1-1) to the compound (1-6-1). More desirable compounds (1) are the compound (1-1-1) and the compound (1-2-1). Desirable compounds (2) are the compound (2-1) and the compound (2-2). More desirable compound (2) is compound (2-2). Desirable compounds (3) are from the compound (3-1-1) to the compound (3-20-1). More desirable compounds (3) are the compound (3-1-1) to the compound (3-5-1), and the compound (3-9-1) to the compound (3-19-1). Particularly preferred compound (3) is compound (3-1-1), compound (3-3-1), compound (3-5-1), compound (3-14-1), compound (3-16- 1) and compound (3-17-1). Desirable compounds (4) are from the compound (4-1-1) to the compound (4-12-1). More desirable compounds (4-4-1) are the compounds (4-1-1) to (4-12-1). Particularly preferred compounds (4) are the compound (4-4-1), the compound (4-7-1), and the compound (4-10-1). Desirable compounds (5) are from the compound (5-1-1-1) to the compound (5-5-1). Particularly preferred compound (5) is compound (5-4-1).

  Sixth, additives that may be mixed into the composition will be described. Such additives are optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, and the like. An optically active compound is mixed with the composition for the purpose of inducing a helical structure of liquid crystal to give a twist angle. Examples of such compounds are compound (6-1) to compound (6-4). A desirable ratio of the optically active compound is approximately 5% by weight or less. A more desirable ratio is in the range of approximately 0.01% by weight to approximately 2% by weight.

In order to prevent a decrease in specific resistance due to heating in the atmosphere or to maintain a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after the device has been used for a long time, oxidation prevention An agent is mixed into the composition.

  A preferred example of the antioxidant is a compound (7) wherein w is an integer of 1 to 9. In the compound (7), preferred w is 1, 3, 5, 7, or 9. Further preferred w is 1 or 7. Since the compound (7) in which w is 1 has high volatility, it is effective in preventing a decrease in specific resistance due to heating in the atmosphere. Since the compound (7) in which w is 7 has low volatility, it is effective for maintaining a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after using the device for a long time. . A desirable ratio of the antioxidant is approximately 50 ppm or more for achieving its effect, and is approximately 600 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 300 ppm.

  Preferred examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Also preferred are light stabilizers such as sterically hindered amines. A desirable ratio in these absorbents and stabilizers is approximately 50 ppm or more for obtaining the effect thereof, and approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.

  A dichroic dye such as an azo dye or an anthraquinone dye is mixed with the composition so as to be adapted to a device having a guest host (GH) mode. A preferred ratio of the dye is in the range of 0.01% by weight to 10% by weight. In order to prevent foaming, an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is mixed with the composition. A desirable ratio of the antifoaming agent is about 1 ppm or more for obtaining the effect thereof, and 1000 ppm or less for preventing a poor display. A more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.

  A polymerizable compound is mixed with the composition in order to adapt to a device having a polymer sustained alignment (PSA) mode. Preferred examples of the polymerizable compound are compounds having a polymerizable group such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), vinyl ketone and the like. Particularly preferred examples are acrylate or methacrylate derivatives. A desirable ratio of the polymerizable compound is approximately 0.05% by weight or more for obtaining the effect thereof, and is 10% by weight or less for preventing a display defect. A more desirable ratio is in the range of approximately 0.1% by weight to approximately 2% by weight. The polymerizable compound is preferably polymerized by UV irradiation or the like in the presence of a suitable initiator such as a photopolymerization initiator. Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature. For example, Irgacure 651 (registered trademark), Irgacure 184 (registered trademark), or Darocure 1173 (registered trademark) (Ciba Japan KK), which is a photopolymerization initiator, is suitable for radical polymerization. The polymerizable compound preferably comprises a photopolymerization initiator in the range of about 0.1% to about 5% by weight. Particularly preferably, the photopolymerization initiator is contained in the range of about 1% by weight to about 3% by weight.

  Seventh, a method for synthesizing the component compounds will be described. These compounds can be synthesized by known methods. The synthesis method is illustrated. Compound (1-1-1) is synthesized by the method described in International Publication No. 2009/034867 pamphlet. Compound (2-1) is synthesized by the method described in JP-A-59-70624. Compound (3-1-1) is synthesized by the method described in JP-T-2-503441. Compound (4-6-1) is synthesized by the method described in JP-T-2006-503130. Compound (5-4-1) is synthesized by the method described in JP-A-2005-290349. Antioxidants are commercially available. A compound of formula (7) where w is 1 is available from Sigma-Aldrich Corporation. Compound (7) etc. in which w is 7 are synthesized by the method described in US Pat. No. 3,660,505.

  Compounds that have not been described as synthetic methods include Organic Syntheses (John Wiley & Sons, Inc), Organic Reactions (John Wiley & Sons, Inc), Comprehensive Organic Synthesis (Comprehensive Organic Synthesis) Synthesis, Pergamon Press) and new experimental chemistry course (Maruzen). The composition is prepared from the compound thus obtained by known methods. For example, the component compounds are mixed and dissolved in each other by heating.

  Finally, the use of the composition will be described. Most compositions have a minimum temperature of about −10 ° C. or lower, a maximum temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20. A device containing this composition has a large voltage holding ratio. This composition is suitable for an AM device. This composition is particularly suitable for a transmissive AM device. A composition having an optical anisotropy in the range of about 0.08 to about 0.25 may be prepared by controlling the ratio of the component compounds or by mixing other liquid crystal compounds. This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.

  This composition can be used for an AM device. Further, it can be used for PM elements. This composition can be used for an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, VA, and PSA. Use for an AM device having an IPS or VA mode is particularly preferable. These elements may be reflective, transmissive, or transflective. Use in a transmissive element is preferred. It can also be used for an amorphous silicon-TFT device or a polycrystalline silicon-TFT device. It can also be used for an NCAP (nematic curvilinear aligned phase) type device produced by microencapsulating this composition, or a PD (polymer dispersed) type device in which a three-dimensional network polymer is formed in the composition.

  In order to evaluate the composition and the compound to be contained in the composition, the composition and the compound are used as measurement objects. When the object to be measured was a composition, it was measured as it was, and the obtained value was described. When the measurement object was a compound, a sample for measurement was prepared by mixing this compound (15% by weight) with mother liquid crystals (85% by weight). The characteristic value of the compound was calculated from the value obtained by the measurement by extrapolation. (Extrapolated value) = {(Measured value of measurement sample) −0.85 × (Measured value of mother liquid crystal)} / 0.15. When the smectic phase (or crystal) is precipitated at 25 ° C. at this ratio, the ratio of the compound and the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight in this order. changed. By this extrapolation method, the maximum temperature, optical anisotropy, viscosity and dielectric anisotropy values for the compound were determined.

The components of the mother liquid crystals and their proportions are as follows.

  The characteristic values were measured according to the following method. Many of them are the method described in the Standard of Electric Industries Association of Japan EIAJ ED-2521A or a modified method thereof.

  Maximum temperature of nematic phase (NI; ° C.): A sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature was measured when a part of the sample changed from a nematic phase to an isotropic liquid. The upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.

Minimum Temperature of a Nematic Phase (T C; ℃): A sample having a nematic phase was put in a glass bottle, 0 ℃, -10 ℃, -20 ℃, then kept for 10 days in a freezer at -30 ° C., and -40 ℃ The liquid crystal phase was observed. For example, when the sample remained in a nematic phase at −20 ° C. and changed to a crystal or smectic phase at −30 ° C., TC was described as ≦ −20 ° C. The lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.

  Viscosity (bulk viscosity; η; measured at 20 ° C .; mPa · s): An E-type rotational viscometer was used for measurement.

  Optical anisotropy (refractive index anisotropy; Δn; measured at 25 ° C.): Measurement was performed with an Abbe refractometer using a light having a wavelength of 589 nm and a polarizing plate attached to an eyepiece. After rubbing the surface of the main prism in one direction, the sample was dropped on the main prism. The refractive index n‖ was measured when the polarization direction was parallel to the rubbing direction. The refractive index n⊥ was measured when the polarization direction was perpendicular to the rubbing direction. The value of optical anisotropy was calculated from the equation: Δn = n∥−n⊥.

Dielectric anisotropy (Δε; measured at 25 ° C.): The value of dielectric anisotropy was calculated from the equation: Δε = ε∥−ε⊥. The dielectric constants (ε‖ and ε⊥) were measured as follows.
1) Measurement of dielectric constant (ε‖): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a well-cleaned glass substrate. The glass substrate was rotated with a spinner and then heated at 150 ° C. for 1 hour. A sample was put in a VA element in which the distance between two glass substrates (cell gap) was 4 μm, and the element was sealed with an adhesive that was cured with ultraviolet rays. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant (ε‖) in the major axis direction of the liquid crystal molecules was measured.
2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. After baking this glass substrate, the obtained alignment film was rubbed. A sample was put in a TN device in which the distance between two glass substrates (cell gap) was 9 μm and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured.

  Threshold voltage (Vth; measured at 25 ° C .; V): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source is a halogen lamp. A sample is placed in a normally black mode VA element in which the distance between two glass substrates (cell gap) is 4 μm and the rubbing direction is anti-parallel, and this element is used with a UV curing adhesive. And sealed. The voltage (60 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 20V by 0.02V. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. A voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum and the transmittance was 0% when the light amount was the minimum. The threshold voltage is a voltage when the transmittance reaches 10%.

  Voltage holding ratio (VHR-1; 25 ° C .;%): The TN device used for the measurement has a polyimide alignment film, and the distance between two glass substrates (cell gap) is 5 μm. This element was sealed with an adhesive polymerized by ultraviolet rays after putting a sample. The TN device was charged by applying a pulse voltage (60 microseconds at 5 V). The decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined. The area B is an area when it is not attenuated. The voltage holding ratio is a percentage of the area A with respect to the area B.

  Voltage holding ratio (VHR-2; 80 ° C .;%): The TN device used for the measurement has a polyimide alignment film, and the distance between two glass substrates (cell gap) is 5 μm. This element was sealed with an adhesive polymerized by ultraviolet rays after putting a sample. The TN device was charged by applying a pulse voltage (60 microseconds at 5 V). The decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined. The area B is an area when it is not attenuated. The voltage holding ratio is a percentage of the area A with respect to the area B.

  Voltage holding ratio (VHR-3; 25 ° C .;%): After irradiation with ultraviolet rays, the voltage holding ratio was measured to evaluate the stability against ultraviolet rays. A composition having a large VHR-3 has a large stability to ultraviolet light. The TN device used for measurement has a polyimide alignment film, and the cell gap is 5 μm. A sample was injected into this element and irradiated with light for 20 minutes. The light source is an ultra high pressure mercury lamp USH-500D (manufactured by USHIO), and the distance between the element and the light source is 20 cm. In the measurement of VHR-3, the decreasing voltage was measured for 16.7 milliseconds. VHR-3 is preferably 90% or more, and more preferably 95% or more.

  Voltage holding ratio (VHR-4; 25 ° C .;%): The TN device injected with the sample was heated in a thermostat at 80 ° C. for 500 hours, and then the voltage holding ratio was measured to evaluate the stability against heat. A composition having a large VHR-4 has a large stability to heat. In the measurement of VHR-4, the decreasing voltage was measured for 16.7 milliseconds.

  Response time (τ; measured at 25 ° C .; ms): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source is a halogen lamp. The low-pass filter was set to 5 kHz. A sample is placed in a normally black mode VA element in which the distance between two glass substrates (cell gap) is 4 μm and the rubbing direction is anti-parallel, and this element is used with a UV curing adhesive. And sealed. A rectangular wave (60 Hz, 10 V, 0.5 seconds) was applied to this element. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. The transmittance is 100% when the light amount is maximum, and the transmittance is 0% when the light amount is minimum. The response time is the time (fall time; milliseconds) required to change the transmittance from 90% to 10%.

  Specific resistance (ρ; measured at 25 ° C .; Ωcm): A sample (1.0 mL) was poured into a vessel equipped with electrodes. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following equation. (Resistivity) = {(Voltage) × (Capacity of container)} / {(DC current) × (Dielectric constant of vacuum)}.

  Gas chromatographic analysis: A GC-14B gas chromatograph manufactured by Shimadzu Corporation was used for measurement. The carrier gas is helium (2 mL / min). The sample vaporization chamber was set at 280 ° C, and the detector (FID) was set at 300 ° C. For separation of the component compounds, capillary column DB-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm; stationary liquid phase is dimethylpolysiloxane; nonpolar) manufactured by Agilent Technologies Inc. was used. The column was held at 200 ° C. for 2 minutes and then heated to 280 ° C. at a rate of 5 ° C./min. A sample was prepared in an acetone solution (0.1% by weight), and 1 μL thereof was injected into the sample vaporization chamber. The recorder is a C-R5A type Chromatopac manufactured by Shimadzu Corporation or an equivalent thereof. The obtained gas chromatogram showed the peak retention time and peak area corresponding to the component compounds.

  As a solvent for diluting the sample, chloroform, hexane or the like may be used. In order to separate the component compounds, the following capillary column may be used. HP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc., Rtx-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Restek Corporation, BP-1 made by SGE International Pty. Ltd (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm). In order to prevent compound peaks from overlapping, a capillary column CBP1-M50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Shimadzu Corporation may be used.

  The ratio of the liquid crystal compound contained in the composition may be calculated by the following method. Liquid crystalline compounds can be detected by gas chromatography. The area ratio of peaks in the gas chromatogram corresponds to the ratio (number of moles) of liquid crystal compounds. When the capillary column described above is used, the correction coefficient of each liquid crystal compound may be regarded as 1. Accordingly, the ratio (% by weight) of the liquid crystal compound is calculated from the peak area ratio.

The present invention will be described in detail by examples. The present invention is not limited by the following examples. The compounds in Comparative Examples and Examples were represented by symbols based on the definitions in Table 3 below.
In Table 3, the configuration regarding 1,4-cyclohexylene is trans. In the examples, the number in parentheses after the symbol corresponds to the compound number. The symbol (−) means other liquid crystal compounds. The ratio (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the total weight of the liquid crystal composition, and the liquid crystal composition contains impurities in addition to this. Finally, the characteristic values of the composition are summarized.

[Comparative Example 1]
Composition Example 4 was selected from the compositions disclosed in International Publication No. 2009/034867. This is based on the fact that this composition is compound (1-1-1), compound (1-3-1), compound (3-2-1), compound (3-5-1), compound (4-1-1). ) And the compound (4-4-1) and has the lowest viscosity. Since there was no description about bulk viscosity, this composition was prepared and it measured by the method mentioned above. The components and properties of this composition are as follows.
5-HH1OB (2F, 3F) H-3 (1-1-1) 6%
5-HH1OB (2F, 3F) B-3 (1-3-1) 5%
3-H2B (2F, 3F) -O2 (3-2-1) 18%
5-H2B (2F, 3F) -O2 (3-2-1) 19%
3-HBB (2F, 3F) -O2 (3-5-1) 7%
5-HBB (2F, 3F) -O2 (3-5-1) 8%
3-HB-O2 (4-1-1) 7%
3-HHB-1 (4-4-1) 5%
V2-HHB-1 (4-4-1) 3%
3-HHB-O1 (4-4-1) 5%
3-H2H-V (-) 17%
NI = 81.4 ° C .; Tc ≦ −20 ° C .; Δn = 0.096; η = 22.3 mPa · s; Δε = −3.4.

[Example 1]
3-HH1OB (2F, 3F) H-5 (1-1-1) 5%
5-HH1OB (2F, 3F) H-3 (1-1-1) 5%
3-HH-V (2-2) 30%
3-H2B (2F, 3F) -O2 (3-2-1) 10%
5-H2B (2F, 3F) -O2 (3-2-1) 20%
2-HHB (2F, 3F) -O2 (3-3-1) 8%
3-HHB (2F, 3F) -O2 (3-3-1) 5%
1V2-HHB (2F, 3F) -O2 (3-3-1) 7%
3-HBB (2F, 3F) -O2 (3-5-1) 5%
5-HBB (2F, 3F) -O2 (3-5-1) 5%
NI = 83.2 ° C .; Tc ≦ −20 ° C .; Δn = 0.085; η = 19.9 mPa · s; Δε = −3.5; VHR-1 = 99.2%; VHR-2 = 98.1 %; VHR-3 = 97.9%.

[Example 2]
2-HH1OB (2F, 3F) H-3 (1-1-1) 5%
V-HH1OB (2F, 3F) H-3 (1-1-1) 5%
3-HH-O1 (2-1) 5%
3-HH-V (2-2) 28%
3-HH-V1 (2-2) 7%
5-HB (2F, 3F) -O2 (3-1-1) 5%
1V2-HB (2F, 3F) -O2 (3-1-1) 7%
3-HHB (2F, 3F) -1 (3-3-1) 5%
3-HHB (2F, 3CL) -O2 (3-6-1) 5%
3-H1OB (2F, 3F) -O2 (3-13-1) 5%
3-HH1OB (2F, 3F) -O2 (3-14-1) 5%
5-HH1OB (2F, 3F) -O2 (3-14-1) 8%
3-HH1OB (2F, 3F) -1 (3-14-1) 3%
3-HDhB (2F, 3F) -O2 (3-17-1) 7%
NI = 84.6 ° C .; Tc ≦ −20 ° C .; Δn = 0.073; η = 19.8 mPa · s; Δε = −3.4; VHR-1 = 99.1%; VHR-2 = 98.0 %; VHR-3 = 97.7%.

[Example 3]
5-HH1OB (2F, 3F) H-O2 (1-1-1) 5%
5-HHEB (2F, 3F) H-3 (1-2-1) 5%
5-HHEB (2F, 3F) H-O2 (1-2-1) 5%
2-HH-3 (2-1) 5%
3-HH-V (2-2) 7%
3-HH-V1 (2-2) 10%
3-HH-VFF (2) 10%
V-HB (2F, 3F) -O2 (3-1-1) 5%
3-H2B (2F, 3F) -O2 (3-2-1) 10%
3-HHB (2F, 3F) -1 (3-3-1) 7%
3-HH2B (2F, 3F) -O2 (3-4-1) 10%
3-HBB (2F, 3CL) -O2 (3-7-1) 3%
3-HH2B (2F, 3F, 6Me) -O2 (3-8-1) 3%
3-H1OB (2F, 3F) -O2 (3-13-1) 5%
5-H1OB (2F, 3F) -O2 (3-13-1) 10%
NI = 82.8 ° C .; Tc ≦ −20 ° C .; Δn = 0.076; η = 19.7 mPa · s; Δε = −3.4; VHR-1 = 99.2%; VHR-2 = 98.0 %; VHR-3 = 98.0%.

[Example 4]
5-HH1OB (2F, 3F) H-3 (1-1-1) 7%
V-HH1OB (2F, 3F) H-3 (1-1-1) 5%
5-HH1OB (2F, 3F) B-3 (1-3-1) 5%
3-HH-V (2-2) 30%
3-HH-V1 (2-2) 3%
3-H2B (2F, 3F) -O2 (3-2-1) 15%
2-HHB (2F, 3F) -O2 (3-3-1) 5%
1V2-HHB (2F, 3F) -O2 (3-3-1) 5%
2O-B (2F) B (2F, 3F) -O3 (3-9-1) 5%
3-HEB (2F, 3F) B (2F, 3F) -O2 (3-12-1) 3%
3-H1OB (2F, 3F) -O2 (3-13-1) 4%
3-HH1OB (2F, 3F) -1 (3-14-1) 3%
3-HB-O2 (4-1-1) 5%
3-HHB-1 (4-4-1) 5%
NI = 83.5 ° C .; Tc ≦ −20 ° C .; Δn = 0.083; η = 18.3 mPa · s; Δε = −3.0; VHR-1 = 99.3%; VHR-2 = 98.1 %; VHR-3 = 98.1%.

[Example 5]
5-HH1OB (2F, 3F) H-3 (1-1-1) 7%
5-HHEB (2F, 3F) H-3 (1-2-1) 5%
5-HHEB (2F, 3F) B-3 (1-4-1) 3%
2-HH-3 (2-1) 10%
3-HH-V (2-2) 20%
3-HH-VFF (2) 5%
2-H1OB (2F, 3F) -O2 (3-13-1) 5%
3-H1OB (2F, 3F) -O2 (3-13-1) 7%
V-H1OB (2F, 3F) -O2 (3-13-1) 7%
5-HH1OB (2F, 3F) -O2 (3-14-1) 5%
5-DhB (2F, 3F) -O2 (3-15-1) 3%
3-HDhB (2F, 3F) -O2 (3-17-1) 5%
3-DhH1OB (2F, 3F) -O2 (3-18-1) 5%
V-HHB-1 (4-4-1) 5%
3-HBB-2 (4-5-1) 3%
2-BB (F) B-3 (4-6-1) 5%
NI = 82.4 ° C .; Tc ≦ −20 ° C .; Δn = 0.082; η = 18.7 mPa · s; Δε = −3.2; VHR-1 = 99.3%; VHR-2 = 98.1 %; VHR-3 = 98.1%.

[Example 6]
V-HH1OB (2F, 3F) H-3 (1-1-1) 6%
5-HHEB (2F, 3F) B-3 (1-4-1) 6%
5-HBEB (2F, 3F) B-3 (1-6-1) 4%
2-HH-3 (2-1) 8%
3-HH-5 (2-1) 5%
3-HH-VFF (2) 10%
3-H2B (2F, 3F) -O2 (3-2-1) 10%
5-HH2B (2F, 3F) -O2 (3-4-1) 12%
2O-B (2F, 3F) B (2F, 3F) -O3 (3-10-1) 3%
3-H1OB (2F, 3F) -O2 (3-13-1) 5%
V-H1OB (2F, 3F) -O2 (3-13-1) 10%
V-BB-1 (4-2-1) 5%
1V2-BB-1 (4-2-1) 3%
3-HHEH-5 (4-3-1) 3%
5-B (F) BB-2 (4-7-1) 5%
3-B (F) BB-2V (4-7-1) 5%
NI = 83.1 ° C .; Tc ≦ −20 ° C .; Δn = 0.109; η = 18.7 mPa · s; Δε = −3.0; VHR-1 = 99.1%; VHR-2 = 98.0 %; VHR-3 = 98.0%.

[Example 7]
5-HHEB (2F, 3F) H-O2 (1-2-1) 6%
5-HBEB (2F, 3F) H-3 (1-5-1) 3%
5-HHXB (2F, 3F) B-3 (1) 3%
3-HH-V (2-2) 12%
3-HH-V1 (2-2) 5%
V-HB (2F, 3F) -O2 (3-1-1) 3%
1V-HB (2F, 3F) -O2 (3-1-1) 5%
3-H2B (2F, 3F) -O2 (3-2-1) 21%
3-HH2B (2F, 3F) -O2 (3-4-1) 3%
2-BB (2F, 3F) B-4 (3-11-1) 5%
2-H1OB (2F, 3F) -O2 (3-13-1) 5%
V-H1OB (2F, 3F) -O2 (3-13-1) 5%
V-BB-1 (4-2-1) 10%
3-HHEBH-3 (4-8-1) 5%
3-HBBH-3 (4-9-1) 3%
3-HB (F) BH-3 (4-11-1) 3%
5-HBB (F) B-2 (4-12-1) 3%
NI = 82.7 ° C .; Tc ≦ −20 ° C .; Δn = 0.106; η = 19.1 mPa · s; Δε = −3.0; VHR-1 = 99.2%; VHR-2 = 98.1 %; VHR-3 = 98.1%.

[Example 8]
5-HH1OB (2F, 3F) H-3 (1-1-1) 5%
5-HH1OB (2F, 3F) H-O2 (1-1-1) 5%
3-HH-V (2-2) 28%
3-HH-V1 (2-2) 7%
V-HB (2F, 3F) -O3 (3-1-1) 4%
3-H2B (2F, 3F) -O2 (3-2-1) 8%
5-HH2B (2F, 3F) -O2 (3-4-1) 12%
V-H1OB (2F, 3F) -O2 (3-13-1) 6%
3-DhHB (2F, 3F) -O2 (3-16-1) 5%
3-dhBB (2F, 3F) -O2 (3-19-1) 5%
3-HH1OB (2F, 3F, 6Me) -O2 (3-20-1) 3%
5-HB (2F, 3CL) -O2 (3) 3%
V-BB-1 (4-2-1) 3%
3-HHEH-5 (4-3-1) 3%
1O1-HBBH-4 (-) 3%
NI = 83.3 ° C .; Tc ≦ −20 ° C .; Δn = 0.081; η = 18.3 mPa · s; Δε = −3.0; VHR-1 = 99.3%; VHR-2 = 98.2 %; VHR-3 = 98.0%.

[Example 9]
V-HH1OB (2F, 3F) H-3 (1-1-1) 3%
5-HHEB (2F, 3F) H-3 (1-2-1) 7%
5-HHEB (2F, 3F) B-3 (1-4-1) 5%
3-HH-V (2-2) 27%
3-HH-V1 (2-2) 7%
3-H2B (2F, 3F) -O2 (3-2-1) 4%
2O-B (2F, 3F) B (2F, 3F) -O4 (3-10-1) 5%
V-H1OB (2F, 3F) -O2 (3-13-1) 5%
5-HH1OB (2F, 3F) -O2 (3-14-1) 4%
V-BB-1 (4-2-1) 9%
1V2-BB-1 (4-2-1) 4%
V2-BB (F) B-1 (4-6-1) 3%
5-HB (F) HH-V (4-10-1) 3%
3-H1OCro (7F, 8F) -5 (5-2-1) 5%
3-HH2Cro (7F, 8F) -5 (5-3-1) 3%
3-HH1OCro (7F, 8F) -5 (5-4-1) 3%
5-HB1OCro (7F, 8F) -5 (5-5-1) 3%
NI = 83.1 ° C .; Tc ≦ −20 ° C .; Δn = 0.097; η = 19.3 mPa · s; Δε = −3.1; VHR-1 = 98.9%; VHR-2 = 97.9 %; VHR-3 = 97.8%.

[Example 10]
V-HH1OB (2F, 3F) H-3 (1-1-1) 7%
5-HH1OB (2F, 3F) H-O2 (1-1-1) 3%
5-BBEB (2F, 3F) B-3 (1) 3%
2-HH-3 (2-1) 5%
3-HH-V (2-2) 19%
3-H2B (2F, 3F) -O2 (3-2-1) 20%
3-HH2B (2F, 3F) -O2 (3-4-1) 8%
5-HH2B (2F, 3F) -O2 (3-4-1) 8%
5-HH1OB (2F, 3F) -O2 (3-14-1) 3%
V-BB-1 (4-2-1) 7%
3-HHB-1 (4-4-1) 4%
V2-HHB-1 (4-4-1) 5%
5-H2Cro (7F, 8F) -5 (5-1-1) 5%
4O-Cro (7F, 8F) H-3 (5) 3%
NI = 82.6 ° C .; Tc ≦ −20 ° C .; Δn = 0.087; η = 19.6 mPa · s; Δε = −3.1; VHR-1 = 98.8%; VHR-2 = 97.9 %; VHR-3 = 97.7%.

  The compositions of Examples 1 to 10 have a large maximum temperature and a small viscosity as compared with Comparative Example 1. Therefore, the liquid crystal composition according to the present invention has more excellent characteristics than the liquid crystal composition disclosed in Patent Document 1.

  High maximum temperature of nematic phase, low minimum temperature of nematic phase, small viscosity, appropriate optical anisotropy, negative large dielectric anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, etc. In the liquid crystal composition, the liquid crystal composition satisfies at least one characteristic or has an appropriate balance regarding at least two characteristics. A liquid crystal display element containing such a composition becomes an AM element having a short response time, a large voltage holding ratio, a large contrast ratio, a long lifetime, and the like, and thus can be used for a liquid crystal projector, a liquid crystal television, and the like.

Claims (24)

  1. Contains at least one compound selected from the group of compounds represented by formula (1) as the first component and at least one compound selected from the group of compounds represented by formula (2) as the second component And a liquid crystal composition having negative dielectric anisotropy.

    Here, R 1 , R 2 , R 3 , and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or any hydrogen is fluorine. And the ring A and the ring B are each independently 1,4-cyclohexylene or 1,4-phenylene; either the ring C or the ring D is 2 , 3-difluoro-1,4-phenylene, the other is 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 3 are independently a single bond, ethylene, or difluoromethyleneoxy. Yes; Z 2 is methyleneoxy, difluoromethyleneoxy, or carbonyloxy.
  2. The liquid crystal composition according to claim 1, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-1) to formula (1-6).

    Here, R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number 2 in which any hydrogen is replaced with fluorine. To 12 alkenyl.
  3.   The liquid crystal composition according to claim 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-1).
  4.   The liquid crystal composition according to claim 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-2).
  5.   The proportion of the first component is in the range of 5% to 40% by weight and the proportion of the second component is in the range of 10% to 95% by weight based on the total weight of the liquid crystal composition. 5. The liquid crystal composition according to any one of 4 above.
  6. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the group of compounds represented by formula (3) as a third component.

    Here, R 5 and R 6 are each independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine. Ring E is independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 2-fluoro-1,4-phenylene, or 2, 3-difluoro-1,4-phenylene; Z 4 is independently a single bond, ethylene, methyleneoxy, or carbonyloxy; X 1 and X 2 are independently fluorine or chlorine; Y 1 is hydrogen or methyl; p is 1 or 2, q is 0 or 1, and the sum of p and q is 2 or less.
  7. The liquid crystal composition according to claim 6, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-1) to formula (3-20).


    Here, R 5 and R 6 are each independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine. To 12 alkenyl.
  8.   The liquid crystal composition according to claim 7, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-1).
  9.   The third component is at least one compound selected from the group of compounds represented by formula (3-2) and at least one compound selected from the group of compounds represented by formula (3-5) The liquid crystal composition according to claim 7.
  10.   The liquid crystal composition according to claim 7, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-14).
  11.   The liquid crystal composition according to claim 7, wherein the third component is at least one compound selected from the group of compounds represented by formula (3-16) to formula (3-19).
  12.   The liquid crystal composition according to any one of claims 6 to 11, wherein the ratio of the third component is in the range of 10 wt% to 70 wt% based on the total weight of the liquid crystal composition.
  13. The liquid crystal composition according to any one of claims 1 to 12, further comprising at least one compound selected from the group of compounds represented by formula (4) as a fourth component.

    Here, R 7 and R 8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number 2 in which any hydrogen is replaced with fluorine. Ring F, ring G, and ring I are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3-fluoro-. 1,4-phenylene; Z 5 and Z 6 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy; r is 0, 1, or 2, where r is 0 , At least one of ring G and ring I is 1,4-phenylene.
  14. The liquid crystal composition according to claim 13, wherein the fourth component is at least one compound selected from the group of compounds represented by formulas (4-1) to (4-12).

    Here, R 7 and R 8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number 2 in which any hydrogen is replaced with fluorine. To 12 alkenyl.
  15.   The liquid crystal composition according to claim 14, wherein the fourth component is at least one compound selected from the group of compounds represented by formula (4-4).
  16.   The liquid crystal composition according to claim 14, wherein the fourth component is at least one compound selected from the group of compounds represented by formula (4-7).
  17.   The liquid crystal composition according to any one of claims 13 to 16, wherein the ratio of the fourth component is in the range of 5 wt% to 40 wt% based on the total weight of the liquid crystal composition.
  18. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the group of compounds represented by formula (5) as a fifth component.

    Here, R 9 and R 10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having an arbitrary hydrogen substituted with fluorine. Ring J and ring K are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or 2,3-difluoro-1,4. -Phenylene; Z 7 and Z 8 are independently a single bond, ethylene, methyleneoxy, or carbonyloxy; s and t are independently 0, 1, 2, or 3, and The sum of s and t is 3 or less.
  19. The liquid crystal composition according to claim 18, wherein the fifth component is at least one compound selected from the group of compounds represented by formulas (5-1) to (5-5).

    Here, R 9 and R 10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having an arbitrary hydrogen substituted with fluorine. To 12 alkenyl.
  20.   The liquid crystal composition according to claim 19, wherein the fifth component is at least one compound selected from the group of compounds represented by formula (5-4).
  21.   21. The liquid crystal composition according to claim 18, wherein the ratio of the fifth component is in the range of 5% by weight to 30% by weight based on the total weight of the liquid crystal composition.
  22.   The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy (25 ° C.) at a wavelength of 589 nm is 0.08 or higher, and the dielectric anisotropy (25 ° C.) at a frequency of 1 kHz is −2 or lower. The liquid crystal composition according to any one of claims 1 to 21.
  23.   The liquid crystal display element containing the liquid-crystal composition of any one of Claim 1 to 22.
  24.   The liquid crystal display element according to claim 23, wherein an operation mode of the liquid crystal display element is a VA mode, an IPS mode, or a PSA mode, and a driving method of the liquid crystal display element is an active matrix method.
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